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Title

Artist

Year

Satta Massagana

Abyssinians

1971

Satta Massagana is one of the most covered tunes in the history of reggae and a rare instance of a song that crossed over into church groups rather than the other way round. Partially sung in Amharic (the title translates as “give praise”), it’s a minor-key classic of close harmonies and the traditional Rastafarian longing for repatriation. It was so far ahead of its time when originally recorded in 1969 that Studio One’s legendary producer Coxsone Dodd rejected it, leaving the song unreleased until the vocal trio formed their own label two years later. SY Listen on Spotify

Dream On

Aerosmith

1973

Still only in his mid-20s, but frustrated by a lack of momentum in his music career, Steven Tyler displayed a Jackson Browne-esque level of maturity-before-his-time when he sang “Every time that I look in the mirror/ All these lines on my face gettin clearer” in Aerosmith’s anthemic debut single from their first album. Those lines would deepen further over the drug-addled next decade, before Tyler’s dreams were finally fulfilled by global popularity in 1987. MR Listen on Spotify

Fluorescent Adolescent

Arctic Monkeys

2007

This wry treatise on female sexual disappointment, co-written, perhaps significantly, by Alex Turner and his ex-girlfriend Johanna Bennett, could be about a woman who settled down too young at 23 or one who has hit a midlife crisis at 43. But that’s a strength that derives from its graceful, old-fashioned melody, and the way the virtuoso lyric glories in the pleasures of witty metaphor and scabrous innuendo. A song for when the “Bloody Mary” of life is sorely “lacking a Tabasco”. GM Listen on Spotify

St James Infirmary Blues

Louis Armstrong

1928

A classic New Orleans funeral blues, in which a rounder discovers his woman has died and he’ll shortly be following her. The machismo with which he plans his own funeral – “Put a twenty-dollar gold piece on my watch chain/ So you can let all the boys know I died standing pat” – contains startling similarities to some of rap’s funeral songs, such as Tupac’s Life Goes On: “Bury me smilin’ with Gs in my pocket.” GT Listen on Spotify

What a Wonderful World

Louis Armstrong

1968

As the US descended into racial and political strife, Impulse! records boss Bob Thiele (a jazz aficionado) decided the country needed something uplifting. Co-written with George Weiss, this two-minute paean to life’s simple pleasures was the result. Its greeting-card sentiments would have turned to goo if sung by anyone but genial toughie Armstrong, and even then it tanked at home while hitting the UK top spot. Now a standard, it was banned by US radio after 9/11; too much irony. NS Listen on Spotify

In My Room

The Beach Boys

1963

It wasn’t all T-Birds and Surfin’ Safaris. The Beach Boys, unlike almost all their contemporaries, understood that the teenage state of mind involved more than parties and break-ups; it was also about solipsism and solitude. That strand would find its fullest expression on Pet Sounds, but In My Room – about a place “I can go and tell my secrets to” – will ring true for as long as adolescents angrily stomp off upstairs. MHa Listen on Spotify

Yer Blues

The Beatles

1968

Lennon’s cosmic blues only serves to add further weight to the darkness at the heart of the Beatles’ sprawling White Album. And while the title might be a distancing device, lest the purists criticise the Fab Four’s foray into a time-honoured musical tradition, there’s no denying that Lennon is talking straight when he states, “(I) Even hate my rock’n’roll” towards the end. Not the death of the Beatles by a long chalk, but certainly a signpost for future honesties. RHJ

Yesterday

The Beatles

1965

As Paul McCartney worked on the aching piano melody that had come to him in a dream, its first working lines were: “Scrambled eggs/ Oh baby, how I love your legs.” Forty-four years later, his ballad about the bitter memories evoked by lost love remains the most covered song of all-time, with more than 3,000 versions and counting. Yesterday was essentially the first Beatles’ solo performance, and was so disliked by Macca’s bandmates that it was initially offered to singer Chris Farlowe. GM

Look Up

Chris Bell

1974

The contrast between Chris Bell and Alex Chilton became clearer when the former left Big Star. In 1974 and 1975, both recorded songs about God: Chilton’s Jesus Christ was a wracked Nativity song, sung from the dregs of his heart – one you won’t be hearing in a primary school come December. Bell’s was filled with hope, encouraging us all to look to the skies, where “He’s the life/ Waiting to love you”. Chilton continues to perform and record; Bell died in a car crash in 1978. MHa

Paranoid

Black Sabbath

1970

Written and recorded in the time it takes to watch an episode of The Osbournes, but still the Sabs’ most famous record, Paranoid was hard rock stripped to a jackhammer riff and primal howl. It also had one of the best opening lines ever – “Finished with my woman ’cause she couldn’t help me with my mind” (oh, the irony) – and a brilliant take on the vague sense of dissatisfaction that runs through rock like a psychic faultline. “Make a joke and I will sigh and you will laugh and I will cry.” There there. SY Listen on Spotify

Happiness

The Blue Nile

1996

They take their time, but they always deliver. From their third album, Peace at Last, this hymn to deep – though transient – contentment is so delicately put together it’s barely there at all. Featuring Paul Buchanan’s wearily ecstatic voice, the gentle tug of an acoustic guitar riff and an atmospheric swirl, it’s so slow, sure and steady that the interjection of the gospel choir at the end is truly explosive. Blue-eyed Scottish soul in excelsis. GT Listen on Spotify

(Don't Fear) The Reaper

Blue Öyster Cult

1976

Blue Öyster Cult’s Donald Roeser, who wrote the band’s biggest hit, was horrified at how people interpreted his song. “It’s basically a love song where the love transcends the actual physical existence of the partners,” he said, dismissing the notion that it was about a suicide pact. Anyone reading the lyrics, however, would say: “Come off it, Don.” The charm of Reaper, however, lies in the disjuncture between its gothic storyline and the sprightly, Byrdsian guitar line that carries it. MHa Listen on Spotify

This Is a Low

Blur

1994

The final track on Parklife, and for a long time the tear-jerking finale at their gigs. Damon Albarn taps into our very British obsession with the weather, lifting the evocative terminology of Radio 4’s comforting shipping forecast. Britpop’s favourite sons strike a contemplative tenor, conjuring the atmosphere of a gloomy English day, when the cold, dismal weather presses in on you but somehow its familiarity is oddly reassuring. SB Listen on Spotify

Kooks

David Bowie

1971

Jaunty enough to be sung to his own newborn son, Kooks rather succinctly addresses the fact that mum and dad aren’t likely to be as normal as other parents and this might rub off on the next generation. OK, son? Purportedly influenced by Neil Young, not to mention British vaudeville, Kooks is whimsical yet direct and remains possibly one of the finer gifts a singer could bestow on a newborn child. RHJ Listen on Spotify

Never Get Old

David Bowie

2003

This skewed, very Scary Monsters-esque rocker from Reality, the most recent of Bowie’s excellent last two records, covers a lot of existential ground; not merely content to rage against the dying of the light, Bowie also slyly nods to his own Dorian Gray act while acknowledging that the human appetite can never be sated: “There’s never gonna be enough money/ Never gonna be enough drugs/ Never gonna be enough sex.” Well, he should know. GT

Bertie

Kate Bush

2005

The arrival of young Bertie in 1998 is the main reason we had to wait 12 years between Kate Bush albums. Still, it sounds like he was worth it. This stately madrigal of devotion to her son may vault the barrier between heartfelt and mawkish, but only a churl could fail to be touched. Just when you think Bush has exhausted her rapture, she finds deeper reserves: “You bring me so much joy/ And then you bring me – more joy!” GT Listen on Spotify

Goin’ Back

The Byrds

1968

“But thinking young and growing older is no sin,” might be the first time pop confronted its inevitable consequence: the creation of a generation mired in permanent adolescence. Proof, if proof were needed, that the Gerry Goffin/Carole King songwriting team knew wisdom, as well as an indelible melody. The latter has attracted a string of performers – Dusty Springfield, Diana Ross, Nils Lofgren – to this song, but it is the Byrds’ performance that captures it in almost hallucinatory clarity. MHa Listen on Spotify

Work

John Cale and Lou Reed

1990

Much of the duo’s Andy Warhol memorial album, Songs for Drella, focuses not on the creativity of the artist but on his capacity for getting on with the job. Over jumpy piano and guitar Reed tells how Warhol would castigate him for not writing enough songs, for not concentrating on building a career, and how he would explain why “the most important thing is work”. It really is perspiration, not inspiration, that counts. CSte

Will the Circle Be Unbroken (By and By)

The Carter Family

1935

The pious hope that “there’s a better home waiting in the sky” is embedded in country music. When bluegrass patriarch AP Carter collected this hymn he left only its chorus, replacing the original with a morbid scenario in which the narrator follows the hearse to his mother’s grave. Endlessly covered, it was made, bizarrely, into a singalong by the Nitty Gritty Dirt Band in 1971. Altogether now: “Undertaker, undertaker, please go slow …” NS

The Mercy Seat

Nick Cave and the Bad Seeds

1988

Cave takes us on that last walk down the Green Mile towards the full blood-boiling horror of the electric chair. Overflowing with biblical allusion, it’s a lyrical tour de force in which the layers of the condemned man’s bravado are peeled away with each verse. Whether played with the Bad Seeds at full throttle or just with a piano accompaniment, this is an intense and vivid record. CSte Listen on Spotify

I’m On My Way to a Better Place

Chairmen of the Board

1972

Gospel has always treated death as a cause for celebration as much as grief, and it’s that tradition that General Johnson draws on for this incredible performance. It begins with his optimistic longing for a world free from hate and prejudice, but it’s only as the angelic choir swells behind him that the true meaning becomes apparent. By the time he’s promising gates made of pearl and streets lined with gold it’s as much as you can do not to jump in the coffin alongside him. SY

If I Could Turn Back Time

Cher

1989

Not all regrets are nuanced; certainly there’s little nuance in the single that cemented Cher’s late-80s comeback. Diane Warren’s lyrics amount to little more than “Sorry. Shouldn’t have said that.” And the video – featuring Cher straddling the 16-inch guns of the USS Missouri – was laughable. But sometimes mediocre songs make incredible records, and this is one: every element – the chugging guitars, the thunderous drums, Cher’s bellow – works to create one of the 80s’ most memorable and, yes, moving power anthems. MHa Listen on Spotify

C’mon Everybody

Eddie Cochran

1958

C’mon Everybody formed one part of a trilogy – alongside Summertime Blues and Somethin’ Else – in which Eddie Cochran codified the idea of the teenager. In Summertime Blues, the teen’s got angst; in Somethin’ Else, the teen’s got lust; but in C’mon Everybody, the teen’s simply bursting with the will to live: “Been a-doin’ my homework all week long/ Now the house is empty and the folks are gone,” and then the most exuberant of hollers: “Whooo! C’mon everybody.” MHa Listen on Spotify

My Favorite Things

John Coltrane Quartet

1961

Made famous by Julie Andrews in the 1965 film version of The Sound of Music and since covered by hundreds of artists, it’s this 13-minute version that really gets under the skin of the song. As drummer Elvin Jones and pianist McCoy Tyner rumble ominously beneath him, Coltrane’s soprano gnaws at the three-note nursery-rhyme melody until it’s transformed into something quite different – a hypnotic, spiritual voyage that ends up higher on the hill than the lonely goat herd. JL Listen on Spotify

School’s Out

Alice Cooper

1972

From its opening, urgent guitar riff to the school bell and screaming kids at the end, this is an impure blast of hormonal exuberance that captures all the craziness of the end of term. The song set up Cooper, a Frank Zappa protege, for a successful career of schlocky horror, and who can fail to smile at the line “We’ve got no class, and we’ve got no principals” – whichever way you spell the final word? CSte Listen on Spotify

Fisherman

The Congos

1977

One of the most profoundly beautiful reggae songs ever made, Fisherman bathes the daily grind in a spiritual light, naming its titular anglers after four of the disciples (dubbed Fishers of Men by Jesus), though it’s not known whether the original apostles also stopped off to see the local collie man. It was produced by Lee Perry (as was the accompanying album, the masterpiece Heart of the Congos), and his prickly dub effects simulated the motion of the waves, alternately calm and crashing. SY Listen on Spotify

My Three Sons

Elvis Costello and the Imposters

2008

It’s hard to imagine a less likely composer of sentimental odes to children than the man stereotyped as Mr Revenge and Guilt, but here is the inconvertible evidence: a simple fireside strum for his toddler twins and grown-up son, with a bittersweet lyric that expresses unbounded love and yet also hints at the lengthening shadows closing in: “I bless the day you came to be,” he sings, “with everything that is left in me.” GT Listen on Spotify

Annie, I’m Not Your Daddy

Kid Creole and the Coconuts

1982

Imagine a Mamma Mia 2! The Brutal Truth, in which the rakish rumoured father of the girl denies all responsibility. He also gives it to her straight about Mum’s time in St Tropez (“Mama was in search of love/ But all she got was used”) and even herself (“If I was in your blood/ You wouldn’t be so ugly”). Bruised feelings are unlikely to be helped by the impossibly infectious Latin pop and jawdropping panache with which this 1982 hit was delivered. MR Listen on Spotify

My Favourite Girl

King Creosote

2005

Fife folkie Kenny Anderson broods over the sombre realisation that time is of the essence as he falls under the shadow of a looming separation from his young daughter. “Promise you’ll tell her she’s my favourite girl,” he sings, in a heartbreakingly simple lyric that churns potently beneath the surface. Deeply moving and exquisitely maudlin, it jerks your heartstrings like they’re flimsy saplings in a force 10 gale. SB Listen on Spotify

That’ll Be the Day

The Crickets

1957

Sung by Buddy Holly and composed by Holly and Crickets’ drummer Jerry Allison (producer Norman Petty’s credit remains disputed), this irresistible beat-pop shuffle took its title and hook from John Wayne’s catchphrase in the classic John Ford western The Searchers. Despite the tune’s friendly jauntiness, the lyric is actually a cruel macho brag – virtually a blueprint for the male domination fantasy of the Stones’ Under My Thumb. GM Listen on Spotify

Killing an Arab

The Cure

1978

Robert Smith translated Camus’s L’Etranger into the language of brittle post-punk on this chilly little assassin, capturing the underlying existential numbness that powered the creative impulse of much of the self-described Blank Generation: “I can turn and walk away/ Or I can fire the gun ... Whichever I chose/ It amounts to the same/ Absolutely nothing.” Following the events of recent years, it’s been rechristened in concert as the achingly PC Killing Another. GT Listen on Spotify

Personal Jesus

Depeche Mode

1989

This much-covered Martin Gore classic was a major shock upon its release. Depeche Mode may have spent the 80s getting away from fey synth-pop, but still no one expected thundering stadium drums, rockabilly guitars and a Dave Gahan vocal of such depth and authority. Inspired by Priscilla Presley’s autobiography, Elvis and Me, Personal Jesus is about the dangers of giving too much power to the lover/mentor in your life. Johnny Cash’s 2002 version lent extra gravitas. GM Listen on Spotify

Fat As a Fiddle

Chris Difford

2008

Squeeze’s master lyricist always excelled in kitchen-sink drama. Here he turns his attentions to the fridge, singing as a well-lunched middle-aged gent panting farewell to the last crumbling vestiges of his previously youthful, lady-killing self in the face of overwhelming physical evidence. Endlessly quotable – “Now I have tits just like my Mum/ I’m out of breath before I run” – Fat As a Fiddle is, literally, the future. GT

Teen Angel

Mark Dinning

1959

Rock’n’roll was laced with tragedy from the start – if it wasn’t dead stars (Holly, Cochran) it was “death discs”. Like Lee Hazlewood’s The Girl on Death Row, Teen Angel echoed like a mausoleum and had a doomed heroine. Her date pulls her clear from the car stalled on the railway track, but she returns for his high school ring. Kaput! Now she watches from “somewhere up above”. This mawkish tale was banned by the Beeb. NS

Sunshine Superman

Donovan

1966

A surprise US No 1, this sublimely funky psych-pop single by Scotland’s Donovan Leitch brought a summery ebullience to both hippie imagery and the art of seduction. Over Jimmy Page’s ringing guitar and a memorable, bluesy bass line, Donovan turns down a trip and compares himself to DC comics superheroes Superman and Green Lantern before opting to “make like a turtle” and dive for pearls for his girl. Marc Bolan was surely taking notes. GM Listen on Spotify

Working in a Coal Mine

Lee Dorsey

1966

Lee Dorsey was already in his 40s when he entered the studio to record Allen Toussaint’s song, and he conveys every possible ounce of world weariness. Unlike that other great American tune about mining, Ernie Ford’s Sixteen Tons, there are no politics here, just a groove (and a dance) that aped the digger’s rhythm and a voice that ached to quit. No stranger to the world of manual labour, Dorsey maintained his own sideline as a mechanic throughout his brilliant career. SY Listen on Spotify

Black Eyed Dog

Nick Drake

1986

Inspired by Winston Churchill’s characterisation of his own depression, Nick Drake’s haunting song, backed by spare guitar with beautiful use of harmonics, was recorded in February 1974 (although not officially released until 1986, on the Time of No Reply compilation), two years after the singer’s Pink Moon album had bombed. He had been drifting between friends’ houses and the family home for some time and his high, haunted vocals speak volumes of the depression, weariness and fear that must have followed him. Nine months later, he was dead from an overdose of antidepressants. MW Listen on Spotify

Not On Top

Herman Düne

2005

Not On Top is less about the reality of middle age than the fear of it. It relates that sense of creeping dread familiar to anyone who’s ever grown a little too attached to their childhood to realise it’s over and the time for big decisions has come. “Feels like I’ll never get my shit together/ 27 and I’m fucked,” sings David-Ivar Herman Düne in his piercing falsetto, before bemoaning the passage of time since Nirvana’s Nevermind changed his adolescent life. SY

Death Is Not the End

Bob Dylan

1988

Dylan once again provides plenty to chew on, offering a song of apparent comfort that’s actually far more ambivalent than it first appears. “When the cities are on fire/ With the burning flesh of men/ Just remember that death is not the end,” he sings. Does death provide a welcome escape from earthly horrors, promising an afterlife of peaceful fulfilment? Or does it usher in another world of eternal pain and suffering? It’s your call. GT

Every Grain of Sand

Bob Dylan

1981

Even fans appalled at Dylan’s conversion to born-again Christianity were won over by this Shot of Love endpiece, which seems to articulate a more universal religiosity. There’s no Satan here, just a gentle melody, a rueful tone and a title apparently quoting Blake’s To See a World in a Grain of Sand. Still, it's Biblical imagery – Cain, “the morals of despair”, “flowers of indulgence”, “the Master’s hand” – that creates a suspicion that behind the poesy lurks another dull sermon. NS

Forever Young

Bob Dylan

1974

The part where Dylan, now with newborn child, gets back together with the Band briefly to reveal a side of him free of acerbic intent. Regarded by many as Dylan’s finest moment, Forever Young is a dream of hope that in many ways warns away from the very cynicism that gave Dylan his bite in the first place. Fatherhood, they say, can do that to a man. RHJ Listen on Spotify

Knockin’ On Heaven’s Door

Bob Dylan

1973

A wisp of a tune that disappears from the soundtrack of Pat Garrett and Billy the Kid almost before it seems to have started, this has become one of the most covered Dylan songs. Both Warren Zevon and Kevin Coyne performed it, on stage and on record, after being diagnosed with terminal illnesses, and even Guns N’ Roses couldn’t bludgeon it into submission. CSte Listen on Spotify

The Lonesome Death of Hattie Carroll

Bob Dylan

1964

Dylan’s so-called “protest songs” were mostly allusive and image-driven, but here he relates a real-life event to devastating effect. Carroll was a black servant who died after a drunken assault by her boss, William Zantzinger, whose subsequent six-month prison sentence became a scandal, if only in liberal circles (he lived a long, affluent life). Slow and painstakingly detailed, the song paints a damning portrait of a still segregated, deeply corrupt south where justice depends on skin colour. NS

Lonelier Than This

Steve Earle

2000

Earle has written far more songs about the vagaries of the human condition than he ever has about politics, and this utterly convincing hymn to wretched solitude is one of the best. Muttered over a sweetly plucked guitar and a rat-a-tat-tat martial drumbeat, it comes from a place where no solace can be found: “It don’t get any lonelier than this,” he sings. “My heartbeat ringing like a hollow drum.” GT

Ebony Eyes

The Everly Brothers

1961

A genuinely sombre, substantial sob song. Look beyond the cheese and there’s something unbearably moving in JD Loudermilk’s tale of a man waiting for his bride-to-be to touch down, only to discover that her plane has crashed. The beacon light from the control tower whipping through the dark skies becomes a haunting image, and you realise that Phil and Don, raised on spooky American music, know a little bit about this death business. GT Listen on Spotify

Summertime

Ella Fitzgerald

1959

The classical critic Alex Ross describes this sombre aria from Gershwin’s 1935 opera as a “steady-state environment in which a gifted performer can move around at will”, bending notes, adding ornaments and so on. Hundreds of artists – from Billie Holiday to Janis Joplin to Rufus Wainwright – have done so, but Ella’s remains the definitive reading. Ira Gershwin’s lullaby lyrics of hope, transcendence and happiness are kept in check by the ominous minor key and by Ella’s magnificently restrained improvisations. JL Listen on Spotify

Regulate

Warren G and Nate Dogg

1994

G-funk dealt in pairing x-rated themes with universal tunes, and Regulate is the very embodiment of the Death Row records sound. The pair trade verses on a ditty that finds Warren G being mugged when Nate Dogg turns up and blows the thieves to bits. The fact that Nate’s cousin Snoop Dogg was on trial for murder at the time did this tune no harm at all on the radio and charts, where it took up long-term residency. Nor did the hook, borrowed from Michael McDonald: rarely have so many sung along so absentmindedly to murder. SY Listen on Spotify

Save the Children

Marvin Gaye

1971

“Who’s willing to save a world/ That is destined to die?” Marvin Gaye and co-composers Al Cleveland and Renaldo Benson cut through the crap to ask the only question that mattered on this heart-stopping highlight from Gaye’s Vietnam war concept album, What’s Going On. The song’s ethereal, symphonic soul construction and the spoken and sung lyric are powerful enough. But when Marvin starts to wail “Save the babies!”, walls – and tears – come tumbling down. GM Listen on Spotify

Glory Hallelujah, How They’ll Sing

Bobbie Gentry

1969

Although it’s just ambiguous enough not to antagonise Bobbie Gentry’s large, hipster audience, Glory Hallelujah sees the Mississippi belle come not to mock southern baptism, but to praise it. It isn’t in itself religious, but a celebration of the role faith plays in binding a community, from sing-songs at a country picnic to the barndance and church. The lyrics are fantastically detailed, and when the ecstatic gospel chorus breaks in, it would take a heart of stone not to feel the rapture. SY

Mind Playing Tricks On Me

Geto Boys

1991

The sharpest analysis of the psychological effects of a criminal lifestyle, created by an uncompromising Houston rap trio best known for their most high-profile member, Bushwick Bill, being a dwarf and having one eye shot out during a domestic. There’s no guns or bling here, though, only paranoia and vulnerability, a sense of constantly looking over one’s shoulder, marking time until it’s your turn to get hurt. GG

So Nice (Summer Samba)

Astrud Gilberto

1966

Written by renowned Brazilian musician Marcos Valle, there’s nothing about this Brazilian cheese-fest that should work – not Walter Wanderley’s rinky-dinky fairground organ, not the drums that lurch from rambunctious samba to Casiotone bossa nova, and certainly not Gilberto’s characteristically naifish, off-key vocals. Yet somehow, it’s impossible to listen to the combined effect of this wonky bossa without ending up with a huge smile on your face. JL Listen on Spotify

Tired of Being Alone

Al Green

1971

There’s a difference between being lonely and being alone, a line that Green crisscrosses here. One moment Al’s a forlorn lover “crying tears”, the next he’s simply a Lonely Heart asking for another date; “meeting you has proven to be my greatest dream” could be a frantic text. If the soul pin-up sounds more interested in himself than his girl, his song’s melodic swoops make up for it. Helps to have a Memphis backing and a brilliant voice, mind. NS

Spirit in the Sky

Norman Greenbaum

1969

A three-time UK No 1 (for Greenbaum, Doctor and the Medics, and Gareth Gates), this bullet-proof song was written after Greenbaum heard Porter Wagoner singing gospel on TV. Its refusal to sombrely observe the traditional tropes of “spiritual” music gives it its affirming kick. Set to a fuzzy, boogie guitar riff, it’s simply a joyous pop single with a sly gospel undertow, the afterlife depicted as the ultimate aftershow party. GT

Workin’ Man’s Blues

Merle Haggard

1969

Haggard’s tribute to the common man arrived alongside his infamous, anti-hippie Okie from Muskogee, and his insistence that “welfare is one place I’ll never be” is either right-wing nonsense or blue-collar pride, depending on your point of view. Later, the Californian country star delivered A Working Man Can’t Get Nowhere Today, a blistering attack on exploitation, but this paean to sweat, beer and babies is more celebrated, and inspired Dylan to pen a song with the same title. NS Listen on Spotify

All Things Must Pass

George Harrison

1970

The title track of Harrison’s bestselling triple album had been rehearsed but not recorded by the Beatles. In its Buddhist-derived acceptance of death and the impermanence of all things, it would have made a fitting end to their career: as it is, George’s plaintive vocal and an almost restrained Phil Spector production combine on a shimmering track that now stands as a memorial to its creator. CSte

I Hear Voices

Screamin’ Jay Hawkins

1962

If sinister vaudevillian Screamin’ Jay Hawkins recorded but one track to rival I Put a Spell On You, it is this brilliant mindbender. Hawkins makes incomprehensible chatterings throughout, which, when set against the discordant keys and dizzying backing vocals, can make even the calmest soul question their sanity. MR Listen on Spotify

Hey Joe

The Jimi Hendrix Experience

1966

Tales of vengeful, gun-toting lovers stalk American song, but Hendrix brought an unrepentant swagger to the role (and a sonic guitar assault). Written by a California folkie, Billy Roberts, Hey Joe was a favourite with west-coast bands, including Arthur Lee’s Love and the Leaves. In old-time ballads such as Little Sadie, the felon is usually brought to justice, but Joe seems destined to slip across the Mexico border and escape the hangman. NS Listen on Spotify

Stuck Between Stations

The Hold Steady

2006

“We drink and we dry up and we crumble into dust/ We get wet and we corrode and we get covered up in rust,” sings Craig Finn in a singularly uplifting hymn to despair. Stuck Between Stations deals, in part, with the suicide of the poet John Berryman, but really it’s about the million profound disappointments of life, about how beneath the apparent hedonism of kids “sucking off each other at the demonstrations”, they’re actually “crushing one another with colossal expectations”. Depression rarely sounds this exciting – because it isn’t, really. MHa Listen on Spotify

Gloomy Sunday

Billie Holiday

1941

Written by László Jávor and set to music by Rezsö Seress (and also known as The Hungarian Suicide Song), this spectacularly morose ballad found fame through Holiday’s recording of Sam Lewis’s English translation and has since been performed by everyone from Mel Tormé to Diamanda Galás. Though there’s scant evidence supporting the legend that the song inspired dozens of real-life suicides, Seress finally followed through on the threat implied in the song: he jumped from his Budapest apartment window in 1968. GT Listen on Spotify

These Important Years

Hüsker Dü

1987

Minneapolis power-trio Hüsker Dü were set apart from the hardcore scene that spawned them: rather than spewing anger outwards, they turned their gaze upon their own lives and emotions (perhaps making them progenitors of emo). These Important Years opened their final album, by which time the band was falling apart, and captures the ennui of being trapped in a life that somehow seems to have gone wrong, warning: “These are your important years, you’d better make them last.” MHa Listen on Spotify

Dead Homiez

Ice Cube

1990

One of the first rap tracks to confront the human reality of black-on-black violence, this thoughtful, heartfelt eulogy to the departed also seethes with anger and almost casually brilliant social commentary: “He got a lot of flowers and a big wreath/ What good is that when you’re six feet deep?” An early and important reminder that rap is – was? – capable of adopting a more reflective attitude to death than it is often given credit for. GT Listen on Spotify

Good Life

Inner City

1988

While the other two of Detroit’s “Belleville Three” (Juan Atkins and Derrick May) were busy shaping techno up as a futurist commentary on their crumbling post-industrial surroundings (in the minds of journalists, anyway), Kevin Saunderson found huge success with a project that had all the unabashed non-intellectualism of its disco ancestor. Good Life, which swiftly followed his very similar Big Fun, was hedonism squared, a celebratory house record paying tribute to celebration itself. SY Listen on Spotify

The Number of the Beast

Iron Maiden

1982

There were those who were outraged by Iron Maiden’s offering to the devil. Why? Even the most cursory inspection of the lyrics reveals The Number of the Beast to be a Hammer Horror storyline set to metal, nothing more. More exciting – and why it remains a stage favourite – is that it’s a clever little song, Clive Burr’s stuttering drums in the verses lending it an air of menace and tension resolved by the descending, fist-pumping chorus. Not scary, just fun. MHa Listen on Spotify

Seasons in the Sun

Terry Jacks

1974

Written by Jacques Brel in 1961, and translated by Rod McKuen, this song was picked up by Jacks, Canadian leader of psychedelic band the Poppy Family, and offered to the Beach Boys before being released as a single. The bastardised, mawkish version of Brel became a monster hit, and the four-note guitar opening is an instant warning that it is probably hard to die when all the birds are singing in the sky. CSte

Needle of Death

Bert Jansch

1965

Jansch’s debut album, recorded on a reel-to-reel at engineer Bill Leader’s home in Camden, contains many treasures, among them this stirring tale of a junkie’s slow descent towards the grave. The story is told straight (if sentimentally) and without metaphor or allusion – “How strange your happy words/ Have ceased to bring a smile from everyone/ How tears have filled the eyes/ Of friends that you once had walked among” – but is no less affecting for that. One from the heart. MW Listen on Spotify

Gun Shot

Anthony Johnson

1982

Jamaica in the early 80s was an economic and political basketcase, but as the music tilted towards the more hedonistic strains of dancehall, some remained committed to cultural lyrics. One such was Anthony Johnson, whose classic Gun Shot was inspired by the police shooting of a Trenchtown man; not by the singular nature of the killing, but because it was an everyday event. The pared-back rhythm and muted horns made room for a pained vocal that owed much to Dennis Brown. SY Listen on Spotify

Losing My Edge

LCD Soundsystem

2002

“I was there in 1974, at the first Suicide practices,” laments the ageing hipster at the centre of Losing My Edge, a spoken-word warning about the dangers of trying too hard. If you’ve replaced your personality with cool reference points, what happens when fashion finally leaves you behind? The answer arrives in the form of a Greek chorus, chanting, “You don’t know what you really want” until the track stumbles to a close. GG Listen on Spotify

Someone Great

LCD Soundsystem

2007

A deliberately ambiguous song about loss, Someone Great maps the demise of a significant relationship, though it is unclear whether the termination is the result of death or simply an irreparable breakdown in communication. The end comes via a phone call, singer James Murphy nailing the anxious mood and putting the listener right next to the receiver with an ominous: “Nothing can prepare you for it, the voice on the other end.” GG Listen on Spotify

Gallows Pole

Led Zeppelin

1970

The “maid freed from the gallows” is a centuries-old staple of folk songs with dozens of variants, but the Zep’s reworking is the most familiar. Acoustic guitar and mandolin then drums, bass and banjo build behind Robert Plant’s bluesy, banshee voice as relatives visit the condemned. Traditionally the hangman is bought off with gold and silver, but in their absence he accepts the felon’s sister’s favours and hangs him anyway, breaking into “see-saw, Marjorie daw” for good measure as the poor chump walks on air. MW

God

John Lennon

1970

At 29 and fresh from the Beatles’ bust-up, Lennon was ready to burn bridges. The finale of his first solo album is a howl of disillusion, disavowing the 60s – “The dream is over” – and rejecting his metaphysical forays in favour of “Yoko and me – that’s reality”. His assertion that “God is a concept by which we measure our pain”, is almost a bonus, borrowed from primal therapy. “If there is a God,” he said at the time, “we’re all it.” Amen to that. NS

Here I Come

Barrington Levy

1985

Justly one of dancehall’s most famous records (even if half its fans think it’s called Broader Than Broadway), Here I Come is actually a jumble of lyrical ideas, through which peeps the story of a woman seeking to unburden herself of her child. “Because you are old and I am young/ And while I’m young, yes I wanna have some fun,” is as good a reason as the father gets. Its impact was huge in the UK, where Jah Screw’s jerky rhythm and squirty effects combined with Levy’s peerless warbling to produce a reggae mainstay. SY Listen on Spotify

Knoxville Girl

The Louvin Brothers

1959

Evolving from the 17th-century ballad The Cruel Miller, this plain depiction of brutal murder in the Appalachians remains the archetypal murder ballad, the ultimate expression of what Nick Cave calls “murderous male attention and nefarious transferred erotic desire”. If the way Ira Louvin sings “I took her by her golden curls and I drug her round and round” doesn’t send shivers down your spine, then you’re made of very strong stuff indeed. GT Listen on Spotify

Alone Again Or

Love

1967

If you are unfortunate enough to stumble across Sarah Brightman’s version of this song, ignore it. Please. Just go to Love’s Forever Changes and listen to the mariachi sweetness of Bryan MacLean’s most wonderful song (and one that seems destined to be always associated with Arthur Lee). Alone Again Or makes being alone sound like joy itself – a rare moment of lightness on a dark and disturbing album. The different between MacLean and Lee might be summed up by this song’s line: “I think that people are the greatest fun.” MHa Listen on Spotify

Baggy Trousers

Madness

1980

One of the Camden Town ska/pop band’s favourite subjects was the growing pains of teenage years. Baggy Trousers is a breathless, bouncing, affectionate ode to harmlessly misspent school days at a 70s north London comprehensive –“oh what fun we had, but didn’t really turn about bad … trying different ways to make a difference to the days” – which still strikes a chord with the Grange Hill generation nearly three decades later. LB

La Tristesse Durera (Scream to a Sigh)

Manic Street Preachers

1993

The title roughly translates as “the sadness will last”, which were reputedly the words of a near-death Van Gogh, but here are the thoughts of a war veteran whose medals mean nothing in old age – they’re merely a “cenotaph souvenir”. Despite the subject matter, this was a minor hit on mid-90s dancefloors, its mighty drums a regular feature of the Chemical Brothers’ DJ sets. GG Listen on Spotify

May You Never

John Martyn

1973

Martyn often dismissed his most famous song as a “lollipop”, but it’s a truly beautiful mix of warm sentiment, wine-drenched vocals and rhythmic finger-picking. Assumed to be about one of his children (though many swear it was written for a drinking buddy), its simple, humble humanity – “May you never lay your head down without a hand to hold” – ensures the universality of its message, and it has attained extra poignancy following Martyn’s recent death. GT Listen on Spotify

Safe from Harm

Massive Attack

1991

Safe from Harm breaks one of pop music’s golden rules, that for “baby” you should always read “lover”. But there’s little doubt that Shara Nelson means an actual gurgling, screaming infant here, coming over all protective in the face of “midnight rockers, city slickers, gunmen and maniacs”. Beneath that cavernous bassline sampled from Billy Cobham, it’s easy to overlook just how magnificent the lyric is, brilliantly distilling the transition from youthful confidence to parental anxiety in a dangerous world. With perfect timing, the Gulf war broke out, forcing a brief abbreviation of the group’s name to Massive. SY Listen on Spotify

Fade to Black

Metallica

1984

Having released one of the fastest, heaviest records ever in debut Kill ’Em All a year earlier, Metallica threw a curveball by including a ballad on 1984’s Ride the Lightning. A first-person depiction of a suicidal man’s thoughts, it unfolds over seven minutes from a delicately picked acoustic intro to a climactic guitar solo at the end. A triumph of light and shade, it showed there was more to Metallica than sheer speed and served as a blueprint for breakthrough single One four years later. PMon

Life’s a Bitch

Nas

1994

A highlight even on Nas’s peerless Illmatic debut, Life’s a Bitch worked its wonders over a smooth groove, but it was the lyrics, shared with friend AZ, that made it such a special moment. From the vantage point of men turning 20, the two reflect on their nihilistic youth, expressed in the hookline “life’s a bitch and then you die, that’s why we get high, cause you never know when you’re gonna go”, before resolving on a more positive outlook. Nas’s father playing trumpet on the track lent added poignancy. SY Listen on Spotify

Feel It (In the Air Tonight)

Naturally 7

2006

The New York a cappella septet, who use voices to imitate all the instruments, found internet fame after performing this drastic reworking of the Phil Collins hit in front of startled commuters on the Paris Métro. It’s more detailed than the minimal original, building on Collins’s chorus a narrative of a fatally wounded gangster getting ready to meet his maker. A fabulously soulful record in its own right, it’s worth the price of entry for two moments of magic: the line “fat lady-type singing like it’s over now” and the beatbox-ed to perfection take on the original’s much-imitated drumroll. SY Listen on Spotify

God’s Song (That’s Why I Love Mankind)

Randy Newman

1972

Leave it to the most sardonic of singer-songwriters to depict the relationship between God and man as a cruel joke, born of the desperate need to believe in something, anything, even if it doesn’t seem to be helping much. Newman’s divinity is both callous and pompous, levelling entire cities then smugly announcing that they “laugh up here in heaven at the prayers you offer me”. Not one to play when the vicar pops round. GG Listen on Spotify

Lithium

Nirvana

1991

At first listen, the third single to be lifted from Nevermind appeared to go against Nirvana’s perceived image as gloomy and pessimistic, its cathartic chorus (essentially just Kurt Cobain singing “Yeah” repeatedly, until hoarse) sounding refreshingly positive, and its quiet-loud-quiet dynamic seemingly made for indie discos the world over. In fact, Cobain was relating the altogether more ambiguous tale of a man’s discovery of religion after the death of his girlfriend. PMon Listen on Spotify

Mo Money Mo Problems

The Notorious BIG

1997

Released a few months after the Notorious BIG’s still-unsolved murder, this followed I’ll Be Missing You to the top of the US chart, providing him with a second posthumous No 1. The title might have seemed prophetic – he was victim of the violence that seemed endemic to hip-hop’s commercial omnipotence during the mid 90s – but the track’s sheer glee suggested the cash was worth any attendant chaos. GG Listen on Spotify

Suicidal Thoughts

The Notorious BIG

1994

Few artistic gestures are as nihilistic as a debut album whose final sound is that of a gunshot-assisted suicide, but that’s how the New York rapper concluded 1994’s Ready to Die. On the phone to mentor Puff Daddy, the Notorious BIG suddenly spins off into depression, regretting a life of pretty crime and treating his dear old mum like dirt. Puff can’t talk him round and there’s only one outcome … GG Listen on Spotify

Alone Again (Naturally)

Gilbert O’Sullivan

1972

So over-freighted with misery is this song that it should collapse into a fit of giggles. The singer has been jilted at the altar, is considering suicide and then, to lighten things up, tells of his parents’ deaths. O’Sullivan’s matter-of-fact tone saves the day. In 1991, his successful case against Biz Markie over a sample from this song changed the law and the course of hip-hop. CSte

Live Forever

Oasis

1994

The third single from Definitely Maybe, Live Forever perfectly encapsulated the infectious, life affirming ambition of Oasis’s debut, and was also the first real indication of Noel Gallagher’s ability to write a simple chorus that engraves itself on the public consciousness. The title came in response to a Kurt Cobain song: “I remember Nirvana had a tune called I Hate Myself and I Want To Die and I was like ‘Well, I’m not having that.” LB

Satan

Orbital

1991

The dance duo’s sample of Sweat Loaf by Texan psychedelic adventurers the Butthole Surfers (“If you see your Mom this weekend, be sure and tell her ... Satan!”) was initially there to mess with ravers’ heads. Live, though, it was accompanied by a montage of tanks, helicopters and general militarism, a comment on human nature that may or may not have been picked up by thousands of revellers in various degrees of “refreshment”. GG

Ms Jackson

OutKast

2000

Ms Jackson was a song with an inbuilt soap opera. Couched as an apology to the mother of André 3000’s former girlfriend, singer Erykah Badu, the mother of his son, Seven, it laid bare the recriminations caused by their split. André bemoans his lack of access, promises to pay the bills and turn up “on the first day of school, and graduation” (what, no school play?). The song marked divorce of another kind, André’s gradual detachment from hip-hop, a development that reached its zenith three years later with The Love Below. SY Listen on Spotify

9 to 5

Dolly Parton

1980

Not only a Grammy-winning US No 1, but a deceptively jaunty anthem of female empowerment (“Pour myself a cup of ambition”) for disaffected working women seeking to climb the career ladder while their male bosses step all over their fingers. Written by Parton for the film of the same name, the music – a febrile mongrel mix of disco and honky-tonk – conveys the sassy message with humour and gusto. GT Listen on Spotify

Another Brick in the Wall, Part II

Pink Floyd

1979

Memory is unreliable, but it suggests this song was inescapable as 1979 turned into 1980. It wasn’t just that Pink Floyd’s first UK single since 1968 was all over radio and TV, which it was – it was that Another Brick in the Wall was sung by every child, in every school playground, at every breaktime, for months on end. They weren’t thinking about what Roger Waters meant by “We don’t need no education” – it was just a statement of generational difference, resonant in its profound simplicity. MHa

Message in a Bottle

The Police

1979

Loneliness and misery were fixtures of the Police’s early years. But Message in a Bottle was the moment they nailed it, turning despair on its head by having the castaway realise that far from being the world’s most isolated, he’s simply one of a hundred million in an identical situation. Call it a song about the broken-hearted or social atomisation, or just one about the Bleach Boys’ own pariah relationship to punk. Either way, this was their first, and deserved, No 1. SY Listen on Spotify

Glory Box

Portishead

1994

Of all the dinner party soundtracks of the 90s, Glory Box is, possibly, the most improbable. Like a lovelorn teen invested with the spirit of the blues, Beth Gibbons, “tired of playing with this bow and arrow”, yearns to be worshipped for her femininity, the harrowing guitars and an Isaac Hayes sample colluding to signify her troubled state of mind. Incredibly, Geoff Barrow, the West Country troupe’s songwriter, thought it “too commercial” to be issued as a single. Happily, the band’s label Go! Discs disagreed. PM Listen on Spotify

Sour Times

Portishead

1994

The other peak of the Bristol collective’s John Barry-meets-hip-hop muse – although Lalo Schifrin is actually the sampled soundtrack composer – this hit single and track from Dummy is an exercise in enigmatic misery. Although the obtuse verses do their best to obscure the theme of lost love, Beth Gibbons’s bereft but sexually charged torch voice repeatedly unleashes a tortured wail of “Nobody loves me, it’s true/ Not like you do”. Guitars twang in threatening agreement. GM Listen on Spotify

Stagger Lee

Lloyd Price

1958

Lee “Stagger Lee” Shelton killed a man in St Louis in 1895 and became an archetypal figure in blues and r’n’b. This stomping version of his tale, driven by sax and doo-wop backing singers, topped the US charts but Price, after a campaign by the Legion of Decency, had to change the words when performing it on TV so that neither gambling nor killing took place. CSte Listen on Spotify

Paranoid Android

Radiohead

1997

The title is typical Yorke self-deprecation, referencing the Hitchhiker’s Guide to the Galaxy’s comically depressed robot, Marvin the Paranoid Android. The rest, though, is a misanthropic brain dump, a stream of anxiety and bitterness that includes the phrase “kicking, screaming, Gucci little piggy”, a dead-eyed put down of a woman whom Yorke witnessed freaking out in a club after someone spilled booze all over her designer frock. GG Listen on Spotify

(Sittin’ On) The Dock of the Bay

Otis Redding

1968

Songs don’t come more poignant than Redding’s posthumous smash. Conceived after his Monterey festival triumph, where the soul star crossed the divide to touch white hearts, Bay was unlike Otis’s previous output – contemplative, without anguish. Recorded shortly before his death, released just afterwards, its rumination on the tides of time made an exquisite, wistful epitaph to a talent that had yet to peak. NS Listen on Spotify

Paint it Black

The Rolling Stones

1966

Mick Jagger once said that this claustrophobic song was the beginning of “miserable psychedelia”, although other beat-boom bands, including the Beatles, were already exploring darker emotions. Brian Jones’s sitar riff shows what an intuitive musician he was, while Jagger’s lyrical rage at the early death of a girlfriend – we don’t know how or why – still chills. CSte Listen on Spotify

I Seen a Man Die

Scarface

1994

The man who rapped on the Geto Boys’ ferocious Mind of a Lunatic has pursued a more thoughtful direction in his solo career, and this slow, smoked-out, sinister southern rap may well be his masterpiece. Like some updated Biblical parable, it tells of man’s inability to feel empathy with his fellow man – and himself – without first wreaking destruction. A chilling work, words and music perfectly in tandem, the end result is truly haunting. GT

Me and Julio Down By the Schoolyard

Paul Simon

1972

Rhymin’ Simon gets his teen self arrested – it’s a serious rap because a “radical priest” has to spring him from jail and then “we was all on the cover of Newsweek”. He bids farewell to his girl Rosie, his home (Corona, Queens) and heads off. Simon’s Latin-tinged hit remains a lovely enigma – just what were he and Julio up to? Drugs? Sex? Gay sex, claimed Truman Capote. Paulie claims he doesn’t know or care. At least, he ain’t telling. NS Listen on Spotify

Feeling Good

Nina Simone

1965

Like Bill Withers’s Lovely Day, Nina Simone’s Feeling Good was destined to reside in the graveyard of great songs murdered by advert overkill until last November, when Obama’s election signalled its sudden reappearance on a million playlists. Originally written for a long-forgotten musical, its celebration of nature’s simple pleasures is timeless enough to be reshaped at the listener’s pleasure, though it’s the power of this rendition by Simone that renders it a civil rights anthem by another name. SY Listen on Spotify

It Was a Very Good Year

Frank Sinatra

1965

Ervin Drake wrote It Was a Very Good Year for the Kingston Trio. But who remembers that version? It took Frank Sinatra recording it for his album September of My Years to make it a standard. This was a perfect match of singer to song: Sinatra shedding the ring-a-ding-ding to embrace gravitas as he looks back at a full life. Better even than the studio recording is the version on Sinatra at the Sands, where the slight cracking in his voice reveals the awareness of mortality that is at the heart of the song’s power. MHa Listen on Spotify

Piss Factory

Patti Smith

1974

With just piano, guitar and voice, Patti Smith created a terrifying portrait of a teenager confronting an adulthood that was not as she had imagined: “Sixteen and time to pay off/ I got this job in a piss factory inspecting pipe.” Her first recording – the B-side to Hey Joe – lays down the themes she would pursue when she had recruited a group: the redemptive power of rock’n’roll, the relish in the complete immersion of the senses in experience, the ecstatic improvisatory flow. It still sounds startling now – goodness knows how those hearing it in 1974 reacted. MHa Listen on Spotify

Dress Sexy at My Funeral

Smog

2000

For those who have yet to discover him, this poignant warning against sinking into matrimonial tedium is a great introduction to the wonderful and unsettling talent of Maryland misanthropist Bill Callahan. It’s bleakly funny, especially when he sings with deadpan relish, “Tell them about the time we did it/ On the beach with fireworks above us.” Better still, it savagely lays bare the conceit of reinventing people’s characters after their death. SB

100%

Sonic Youth

1992

“Can you forgive the boy who shot you in the head, or should you get a gun and get revenge?” sings Sonic Youth’s Thurston Moore to deceased friend and Black Flag roadie Joe Cole, murdered outside his and Henry Rollins’s house in Venice Beach, California. A heavy, mid-tempo stomp, 100% is part eulogy, part blinded fury and is complemented by one of the band’s freest guitar and feedback sessions. Oddly it’s still pop to many ears. RHJ Listen on Spotify

No Surrender

Bruce Springsteen

1984

Perhaps the ultimate expression of one of rock’s great articles of faith: the vow of eternal brotherhood, from schoolyard to graveyard. It’s hard not to hear it as a song about the enduring bond between the Boss and his faithful sidekick Steve Van Zandt, who “learned more from a three-minute record than we ever learned in school”. Adopted by John Kerry as his 2004 election anthem, the solo acoustic version featured on Live: 1975-1985 cuts deepest. GT Listen on Spotify

O Death

Ralph Stanley

2000

Stanley’s a cappella reading of this Appalachian dirge unfolds as an evocative two-hander between the narrator and a merciless Reaper, impervious to emotional pleas. Its roots are centuries old, but the final version was written by Lloyd Chandler, a Baptist preacher from North Carolina, in 1916. Aged over 70, bluegrass legend Stanley recorded the song for the Coen Brothers’ film O Brother, Where Art Thou? and it has since sold around 10m copies; a strangely comforting thought. GT

Once in a Lifetime

Talking Heads

1980

Once in a Lifetime is about about an existential crisis and, suitably, there’s tension everywhere – between David Byrne’s anxious lyric, about the mid-life confusion of a salary man, and the joyous, Fela Kuti-inspired rhythm track; between the sudden self-awareness of its protagonist and the trance-like pull of the music that surrounds him; even between the sanguine call of the verses and panicked response of the chorus. In fact, just listening to it can make you nervous. GG Listen on Spotify

Psycho Killer

Talking Heads

1977

The song that established David Byrne’s public persona – tense, nervous, unhinged – is anchored by Tina Weymouth’s memorable bassline and has a three-line chorus in English, French and gibberish. We don’t know if the disturbed protagonist has killed anyone – but it’s clear he thinks he has. Which probably makes it even more uneasy ... CSte Listen on Spotify

This Is the Day

The The

1983

One of the most outstanding chroniclers of the modern age and much needed once again, Matt Johnson’s The The project had a brush with pop stardom with This Is the Day, their biggest hit. Scratch beneath the surface of the lyrics, however, and you’ll find the song is a fevered battle between a closely intertwined fatalism and optimism. Bittersweet might be a phrase commonly used in pop but rarely has it been so accurately realised by a British artist. RHJ Listen on Spotify

Wish Someone Would Care

Irma Thomas

1964

Wish Someone Would Care was the first song this phenomenal New Orleans soul singer ever wrote herself. It’s a missive from the edge of despair, the lyrics almost a stream of consciousness from a woman whose first marriage was on the slide and career was going nowhere. By the end she’s even given up rhyming (unheard of in soul) as she breaks down at the terrible unfairness of it all. Asked why she never wrote again, she told writer Gerri Hershey: “I don’t ever want to get that mad again.” SY Listen on Spotify

The End of the Rainbow

Richard and Linda Thompson

1974

A cot-side lullaby of crushing despair that begins: “I feel for you, you little horror/ No lucky break for you around the corner,” and then proceeds to get really grim. Written shortly after the birth of the Thompsons’ first child, Muna, this minor-chord lament captures the dreadful flipside of all that postnatal euphoria: that inevitable moment when a parent asks: “What kind of world have I brought you into?” GT Listen on Spotify

I Ain’t Mad at Cha

Tupac

1996

Sung from the perspective of a man whose criminal past has proved fatal, this is a sanguine goodbye, intended for an old friend who had the sense to go straight. What might seem like cliche is rendered poignant by the accompanying video, featuring Tupac in a cheesy heaven filled with lookalikes of Miles Davis, Marvin Gaye and Louis Armstrong. It would be the last he made before his death. GG Listen on Spotify

Hail Mary

Tupac - as Makaveli

1997

A grim premonition of the rapper’s own death, recorded in August 1996, a month before his murder in Las Vegas, but released a year later. Beneath the macho posturing is a man resigned to his fate, who realises he’s just as likely to meet a nasty end on the street as he was inside the prison he has not long left. By this point his life was so steeped in violence that potential enemies were everywhere: there was no way out. GG Listen on Spotify

Exit

U2

1987

The most musically intense and lyrically confrontational track U2 had attempted to that point, the penultimate track on The Joshua Tree is a fanatical, delusional interpretation of God’s will taken to obsessive ends. The killer in the song has something of Rev Harry Powell about him, Robert Mitchum’s crazed preacher in the 1955 movie The Night of the Hunter – a man who, as the song puts it, got “the cure” but went “astray”. Discothèque it ain’t. GT Listen on Spotify

One

U2

1992

The most impressive fusion of Bono’s twin faiths: Christianity and rock’n’roll. Compassion, forgiveness, redemption, the power of platonic love – all are alluded to in that slightly vague way best suited to stadium rock. Allied to a cracking chorus, it’s the U2 mission statement in four and a half minutes, basically. And if you don’t believe rock’n’roll can heal the world, Johnny Cash’s cover is rich in wisdom that’s been earned the hard way. GG Listen on Spotify

Walk Like a Man

Frankie Valli and the Four Seasons

1963

With its unforgettable drumroll, excitable handclaps and impossibly immature vocals (the Four Seasons’ bass singer, Nick Massi, sounds like one of the Dead End Kids, though he was anywhere between 28 and 36) Walk Like a Man is a Be My Baby for boys. There are better ways of putting an ex behind you than jeering, “My own father says give her up, don’t bother/ The world isn’t coming to an end,” and when Frankie Valli’s outrageous falsetto takes on the title, you can almost hear him welling up inside. But this nails adolescence like acne. SY Listen on Spotify

Jesus

The Velvet Underground

1969

The marvel of Lou Reed’s writing in Jesus is that the song works equally well when performed by the Velvets – no one’s idea of a God-fearing churchgoers – and by born-again Christian Glen Campbell, who recorded it last year. It’s barely a song at all, just three different lines, but context is all. When Reed sings “Help me in my weakness/ ’Cause I’m falling out of grace” one hears it as a plea from the gutter for rescue. When Campbell sings it, the line becomes an acknowledgment of humankind’s frailty. MHa Listen on Spotify

Rufus Is a Tit Man

Loudon Wainwright III

1975

No musical dynasty has bared family squabbles with the candour of the Wainwright-McGarrigles. Loudon greeted the arrival of his and Kate’s firstborn with a ditty of naked parental jealousy, gazing at his son “sucking on a nipple, sweeter than the Ripple wine”. Later he would write Daughter, Rufus would snipe back with Dinner at Eight, and Martha with Bloody Mother Fucking Asshole. The irony, of course, is that gay icon Rufus turned out not to be a tit man at all. NS Listen on Spotify

Martha

Tom Waits

1973

Even before he’d truly found his artistic voice, the young Tom Waits was trying out different characters for size. Here, on his debut album, Closing Time, he takes on the role of Tom Frost, weakening just enough to pick up the phone to call an old flame after many years. What could so easily be maudlin is made poetic partly because of Waits’s performance but moreover because even then he was a master of understanding the frailty of romance, treating characters with deserved dignity. RHJ Listen on Spotify

You in the Sky

The Waterboys

2006

Recorded during the mammoth Fisherman’s Blues sessions (it finally appeared on the album’s 2006 deluxe edition, and was later re-recorded for 2007’s Book of Lightning) this is perhaps the most thrilling of Mike Scott’s many conversations with the man upstairs, documenting the triumphs, doubts and frustrations that define the spiritual quest. The music is prime-period Waterboys, all towering sax and searing fiddle, the big music thrillingly shackled to the folk train. GT

Frankie and Johnny

Mae West

1928

Its origins are contested, the consenus being the song was based on the murder of Al Britt by Frankie Baker in 1899 St Louis, Al possibly being Frankie’s pimp (it’s often Frankie and Albert). A popular blues number, it became a signature tune for Mae West, who showcased it in her play Diamond Lil. There are hundreds of versions and variants, but all agree “He was her man and he was doing her wrong”. Some things never change. NS

23 Years Ago

Paul Westerberg

2004

The former Replacement’s solo career has been entertainingly patchy, but this tearfully dishevelled, musical midlife crisis is a highlight. Plagued by guilt and regret, Westerberg confronts the festering sore of an eternal will-we-won’t-we relationship that long ago passed the point of ever being fulfilled. “Our paths cross again and again/ Sometimes five years in between/ There’s one thing goes unsaid ... Maybe you were the one.” Hear it and weep. GT Listen on Spotify

Grandma’s Hands

Bill Withers

1971

Although this song is about all the good uses grandma put her hands to, it’s her relationship with the church that really defines it. Like the best of Withers’s output, it’s tantalisingly short and deceptively simple, never quite breaking into the big gospel hook that’s lurking round the corner. Instead, we’re left with the image of a woman devoting her life to banging her tambourine on Sundays and doing unto others as she’d have others do unto her. SY Listen on Spotify

My Death

Scott Walker

1967

Scott Engel’s fascination with all things Jacques Brel reached a crescendo early on with this take on Brel’s La Mort, in many ways creating the definitive version (for English-speaking countries, at least). Beautiful arrangements by Wally Stott give the piece a classic 60s swing, but there’s no mistaking that Scott Walker’s real interests in the song lie in the fatalism of the lyrics. Walker would later move into even darker waters – which is saying something. RHJ Listen on Spotify

Moon On Your Pyjamas

Paul Weller

1993

A soppy ode to the transformative powers of fatherhood, Weller thanking his son Natt for giving him an optimistic streak (“You got the moon on your pyjamas/ The stars in your eyes/ Sweet child, you’re a dream in disguise”). Inevitably, Natt grew up to be an outrageous goth, keen on Marilyn Manson. Meanwhile, dad wrote about his kids once again on Why Walk When You Can Run, from last year’s 22 Dreams album. GG

I’m So Lonesome I Could Cry

Hank Williams

1949

Hank doesn’t even bother letting us know the cause of his woe (though it’s a safe bet wife Audrey is involved); here loneliness is a given, a fact of life in which nature itself conspires. Through the longest night, robins weep, leaves die and the moon hides. The song was Hank’s favourite, though he fretted his audience would find lines such as “the silence of a falling star” too fancy, and it was stuck on a B-side to await posthumous recognition. NS Listen on Spotify

My Son Calls Another Man Daddy

Hank Williams

1950

This sorrowful wail from an imprisoned parent may have sounded more authentic coming from Lefty Frizzell. Hank’s spells in jail were always short and both the wealth and fame he acquired in his lifetime ensured that putative offspring, of which there were several, were not likely to “never know my name nor my face”. Outrageously dark by anyone else’s standards, for Williams this is pretty typical. Hank mines the depths of despair as only he can. MR Listen on Spotify

Don’t You Worry ‘Bout a Thing

Stevie Wonder

1973

“Y’know I speak very, very, um, fluent Spanish,” Stevie’s protagonist brags during the intro. The stumbling attempts that follow prove otherwise, but the ensuing song proves that he’s entirely fluent in Nuyorican salsa. Despite the lyric’s exhortations to chill out and take it easy, the musical accompaniment becomes increasingly frenetic, with Stevie’s vocal leaping up an octave on the second chorus as he provides his own backing vocals and piles in the Latin percussion. JL

Germ Free Adolescents

X-Ray Spex

1978

Poly Styrene was a pop star of rare talent and even rarer courage. Mixed-race when it was anything but fashionable, she attacked conformism and consumerism in her songs, of which Germ Free Adolescents was the most successful. Delivered as a slow lament, itself a bold statement in punk’s intolerant heyday, it details the obsessive teeth-cleaning, deodorised, sterilised existence of a numbed teenager lost somewhere between Howard Hughes-ish OCD and the body fascism of the Heat generation. Demonstrating her own weary indifference to it all, Poly wore braces on her teeth. SY Listen on Spotify

Old Man

Neil Young

1972

No one will learn too much about the ageing process by listening to Old Man: lyrically it amounts to little more than Neil Young reflecting that because he’s alone, he’s a lot like an old man. But here the message is in the music. Young’s customary dum-dum-thud rhythm is softened by acoustic and slide guitars and mandolin to create a mood of reflective melancholy. In Laurel Canyon they probably thought this was the sound of the pension queue. MHa Listen on Spotify

Keep Me In Your Heart

Warren Zevon

2003

It’s hardly surprising that a songwriter as scabrous as Warren Zevon would have written about dying. More surprising, however, is that Keep Me in Your Heart was written when Zevon was dying of cancer. Gone is the vicious humour of the songs that made him famous, replaced by the simplest of longings – to be remembered fondly. The edge is added by the knowledge that Zevon’s life had not been one to make those who loved him happy; he understands that there’s at least a possibility his plea will be ignored. MHa